Preheat oven to 350°F. Line two cupcake trays with liners. Set aside
In a large bowl, beat together the butter, oil, and sugar until light and completely combined.
Add eggs, one at a time, beating after each addition, then the vanilla extract. Set aside.
In a medium-sized bowl, stir together the flour, baking powder, cinnamon and salt.
Gently fold half of the flour mixture into the butter mixture, then the milk, then the remaining flour mixture.
Portion 1 scoop (approximately 1 to 1 ½ Tablespoons) of batter into each cupcake liner and bake for 5 minutes.
Remove the cupcakes from the oven and place 1 Tablespoon of cherry pie filling in the center of the cupcake. Cover the cupcakes with remaining cupcake batter (approximately 1 ½ Tablespoons each).
Bake for 12-15 minutes, until the cupcakes are completely set and an inserted toothpick comes out without any wet cake batter.
While the cupcakes are cooling, prepare your vanilla cinnamon frosting.